WO2003070830A1 - Lactam-based pigments and the use thereof in the production of coloured plastics or polymeric colour particles - Google Patents

Lactam-based pigments and the use thereof in the production of coloured plastics or polymeric colour particles Download PDF

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Publication number
WO2003070830A1
WO2003070830A1 PCT/EP2003/001426 EP0301426W WO03070830A1 WO 2003070830 A1 WO2003070830 A1 WO 2003070830A1 EP 0301426 W EP0301426 W EP 0301426W WO 03070830 A1 WO03070830 A1 WO 03070830A1
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Prior art keywords
formula
pigment
aryl
conh
coo
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PCT/EP2003/001426
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French (fr)
Inventor
Jean-Marie Adam
Jean-Pierre Bacher
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Ciba Specialty Chemicals Holding Inc.
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Priority to JP2003569734A priority Critical patent/JP2005517792A/en
Priority to AU2003208847A priority patent/AU2003208847A1/en
Priority to US10/502,707 priority patent/US7022177B2/en
Priority to EP03706496A priority patent/EP1476505B1/en
Priority to KR10-2004-7013063A priority patent/KR20040096601A/en
Priority to AT03706496T priority patent/ATE553160T1/en
Publication of WO2003070830A1 publication Critical patent/WO2003070830A1/en

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0091—Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0075—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of an heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C09B23/102—The polymethine chain containing an even number of >CH- groups two heterocyclic rings linked carbon-to-carbon

Definitions

  • Lactam-based pigments and the use thereof in the production of coloured plastics or polymeric colour particles are Lactam-based pigments and the use thereof in the production of coloured plastics or polymeric colour particles
  • the present invention relates to novel lactam-based pigments, to a process for the preparation of those pigments, and to their use in the production of coloured plastics or polymeric colour particles.
  • the present invention accordingly relates to pigments of formula
  • R 1 is hydrogen or CrC ⁇ alkyl
  • R 2 is hydrogen, -CN, -COO-aryl, -COO-heteroaryl, -CONH-aryl or -CONH-heteroaryl, and
  • R 3 is the radical of a heteroaromatic compound of formula or
  • R 4 and R 5 are each independently of the other -CN, -COO-aryl, -COO-heteroaryl,
  • R 6 is a radical of formula
  • R 7 is halogen
  • R 8 and R 9 are each independently of the other C 1 -C 4 alkyl.
  • C r C 12 aIkyl is, for example, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl or dodecyl.
  • Aryl in -COO-aryl and -CONH-aryl in R 2 , R 4 and R 5 is each independently of any other, for example, phenyl which is unsubstituted or substituted by methyl or by halogen, especially by chlorine.
  • Heteroaryi in -CONH-heteroaryl and -COO-heteroaryl in R 2 , R 4 and R 5 is each independently of any other, for example, pyrrole, furan, thiophene, pyridine, imidazole, thiazole, piperazine or pyrimidine.
  • R. is hydrogen or C C 6 alkyl. Special preference is given to R 1 being hydrogen.
  • R 2 is hydrogen or -CN.
  • R 2 being hydrogen
  • R 4 is hydrogen or -CN.
  • R 4 being hydrogen
  • R 5 is hydrogen or -CN.
  • R 5 being hydrogen
  • R 7 is preferably chlorine.
  • R 8 and R 9 as C C 4 alkyl are each independently of the other methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl or, especially, tert-butyl.
  • the present invention relates also to the preparation of pigments of formula (1).
  • Preparation of pigments of formula (1) according to the invention is carried out, for example, by reacting a compound of formula
  • the present invention relates also to a method of producing coloured plastics or polymeric colour particles, which comprises mixing a high molecular weight organic material and a tinctorially effective amount of at least one pigment of formula (1) with one another.
  • the colouring of high molecular weight organic substances with the pigment of formula (1) is carried out, for example, by admixing such a pigment with the substrates using roll mills or mixing or grinding apparatuses, as a result of which the pigment is dissolved or finely dispersed in the high molecular weight material.
  • the high molecular weight organic material together with the admixed pigment is then processed using methods known perse such as, for example, calendering, compression moulding, extrusion, coating, spinning, pouring or injection moulding, as a result of which the coloured material obtains its final form.
  • Admixture of the pigment can also be effected immediately prior to the actual processing step, for example by continuously and simultaneously feeding a solid pigment, for example in powder form, and a granulated or pulverulent, high molecular weight organic material and, optionally, also additional ingredients, such as, for example, additives, directly into the intake zone of an extruder wherein mixing occurs just before processing.
  • a solid pigment for example in powder form
  • additional ingredients such as, for example, additives
  • plasticisers In order to produce non-rigid shaped articles or to reduce their brittleness, it is frequently desirable to add so-called plasticisers to the high molecular weight compounds prior to shaping.
  • plasticisers for example, esters of phosphoric acid, phthalic acid or sebacic acid.
  • the plasticisers can be incorporated into the polymers before or after incorporation of the colorant. It is furthermore possible, in order to achieve different colour shades, also to add to the high molecular weight organic substances, in addition to the pigment of formula (1), further pigments or other colorants in any amounts, optionally together with further additives such as, for example, fillers or siccatives.
  • thermoplastic plastics especially in the form of fibres.
  • Preferred high molecular weight organic materials that can be coloured in accordance with the invention are very generally polymers having a dielectric constant > 2.5, especially polyester, polycarbonate (PC), polystyrene (PS), polymethyl methacrylate (PMMA), polyamide, polyethylene, polypropylene, styrene/acrylonitrile (SAN) and acrylonitrile/buta- diene/styrene (ABS).
  • polyester and polyamide especially preferred are polyester and polyamide.
  • linear aromatic polyesters which can be obtained by polycondensation of terephthalic acid and glycols, especially ethylene glycol, or condensation products of terephthalic acid and 1 ,4-bis(hydroxymethyl)cyclohexane, such as, for example, polyethylene terephthalate (PET) or polybutylene terephthalate (PBTP), and also polycarbonates, for example those obtained from ⁇ , ⁇ -dimethyI-4,4-dihydroxy- diphenylmethane and phosgene, or polymers based on polyvinyl chloride and on polyamide such as, for example, polyamide 6 or polyamide 6.6.
  • the pigments according to the invention impart tinctorially strong shades to the above- mentioned materials, especially the polyester and polyamide materials, with very good in-use fastness properties, these especially being good light-fastness and good thermal stability.
  • polyester granules (PET Arnite D04-300, DSM) are dried at 130°C for 4 hours and then mixed with 0.24 part of the pigment of formula
  • the homogeneous mixture is extruded in an extruder (twin screw 25 mm, from the company Collin, D-85560 Ebersberg) having 6 heating zones, at a maximum temperature of 275°C, cooled with water, granulated in a granulator (Turb Etuve TE 25 from the company MAPAG AG, CH-3001 Bern) and then dried at 130° for 4 hours, resulting in yellow-coloured polyester granules having good all-round fastness properties, especially having very good light and high-temperature-light fastness properties.
  • an extruder twin screw 25 mm, from the company Collin, D-85560 Ebersberg
  • a granulator Teurb Etuve TE 25 from the company MAPAG AG, CH-3001 Bern

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

The present invention relates to novel pigments of formula (1), wherein R1 is hydrogen or C1C12alkyl, -R2 is hydrogen, -CN, -COO-aryl, -COO-heteroaryl, -CONH-aryl or -CONH-heteroaryl, and R3 is the radical of a heteroaromatic compound of formula (II) or (III) or R2 and R3 together form a radical of formula (IV) wherein R4 and R5 are each independently of the other -CN, -COO-aryl, -COO-heteroaryl, -CONH-aryl or -CONH-heteroaryl, R6 is a radical of formula (V), (VI) R7 is halogen, and R8 and R9 are each independently of the other C1-C4alkyl, to a process for the preparation of those pigments, and to their use in the production of coloured plastics or polymeric colour particles.

Description

Lactam-based pigments and the use thereof in the production of coloured plastics or polymeric colour particles
The present invention relates to novel lactam-based pigments, to a process for the preparation of those pigments, and to their use in the production of coloured plastics or polymeric colour particles.
Methods for colouring synthetic materials, such as plastics and polymeric colour particles, in the mass, using pigments, are known. It has been found, however, that the pigments used in such a method do not always fully meet the highest demands, especially with respect to fastness to light, thermal stability and/or tinctorial strength; nor do they completely cover the entire palette of shades desired. There is accordingly a need for new pigments that yield light-fast, thermally stable and tinctorially strong colorations, especially in the yellow to red colour range, and that exhibit good general fastness properties.
It has now been found, surprisingly, that the pigments according to the invention substantially meet the above criteria.
The present invention accordingly relates to pigments of formula
Figure imgf000003_0001
wherein
R1 is hydrogen or CrC^alkyl,
R2 is hydrogen, -CN, -COO-aryl, -COO-heteroaryl, -CONH-aryl or -CONH-heteroaryl, and
R3 is the radical of a heteroaromatic compound of formula
Figure imgf000004_0001
or
R2 and R3 together form a radical of formula
Figure imgf000005_0001
wherein
R4 and R5 are each independently of the other -CN, -COO-aryl, -COO-heteroaryl,
-CONH-aryl or -CONH-heteroaryl,
R6 is a radical of formula
Figure imgf000005_0002
R7 is halogen, and R8 and R9 are each independently of the other C1-C4alkyl.
R., as CrC12aIkyl is, for example, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl or dodecyl.
Aryl in -COO-aryl and -CONH-aryl in R2, R4 and R5 is each independently of any other, for example, phenyl which is unsubstituted or substituted by methyl or by halogen, especially by chlorine.
Heteroaryi in -CONH-heteroaryl and -COO-heteroaryl in R2, R4 and R5 is each independently of any other, for example, pyrrole, furan, thiophene, pyridine, imidazole, thiazole, piperazine or pyrimidine.
Preferably, R., is hydrogen or C C6alkyl. Special preference is given to R1 being hydrogen.
Preferably, R2 is hydrogen or -CN.
Special preference is given to R2 being hydrogen.
Preferably, R4 is hydrogen or -CN.
Special preference is given to R4 being hydrogen.
Preferably, R5 is hydrogen or -CN.
Special preference is given to R5 being hydrogen.
R7 is preferably chlorine.
R8 and R9 as C C4alkyl are each independently of the other methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl or, especially, tert-butyl.
The present invention relates also to the preparation of pigments of formula (1). Preparation of pigments of formula (1) according to the invention is carried out, for example, by reacting a compound of formula
Figure imgf000007_0001
with a compound of formula
Figure imgf000007_0002
wherein
X is =NH or =O, to form a compound of formula
Figure imgf000007_0003
and optionally, when X is =NH, further reacting the compound of formula (52) with an active- methylene compound, for example of formula R4 - CH2 - R5.
The present invention relates also to a method of producing coloured plastics or polymeric colour particles, which comprises mixing a high molecular weight organic material and a tinctorially effective amount of at least one pigment of formula (1) with one another.
The colouring of high molecular weight organic substances with the pigment of formula (1) is carried out, for example, by admixing such a pigment with the substrates using roll mills or mixing or grinding apparatuses, as a result of which the pigment is dissolved or finely dispersed in the high molecular weight material. The high molecular weight organic material together with the admixed pigment is then processed using methods known perse such as, for example, calendering, compression moulding, extrusion, coating, spinning, pouring or injection moulding, as a result of which the coloured material obtains its final form. Admixture of the pigment can also be effected immediately prior to the actual processing step, for example by continuously and simultaneously feeding a solid pigment, for example in powder form, and a granulated or pulverulent, high molecular weight organic material and, optionally, also additional ingredients, such as, for example, additives, directly into the intake zone of an extruder wherein mixing occurs just before processing. Generally, however, it is preferable to mix the pigment into the high molecular weight organic material beforehand, since more uniformly coloured products can be obtained.
In order to produce non-rigid shaped articles or to reduce their brittleness, it is frequently desirable to add so-called plasticisers to the high molecular weight compounds prior to shaping. There may be used as plasticisers, for example, esters of phosphoric acid, phthalic acid or sebacic acid. In the method according to the invention, the plasticisers can be incorporated into the polymers before or after incorporation of the colorant. It is furthermore possible, in order to achieve different colour shades, also to add to the high molecular weight organic substances, in addition to the pigment of formula (1), further pigments or other colorants in any amounts, optionally together with further additives such as, for example, fillers or siccatives.
Preference is given to the colouring of thermoplastic plastics, especially in the form of fibres. Preferred high molecular weight organic materials that can be coloured in accordance with the invention are very generally polymers having a dielectric constant > 2.5, especially polyester, polycarbonate (PC), polystyrene (PS), polymethyl methacrylate (PMMA), polyamide, polyethylene, polypropylene, styrene/acrylonitrile (SAN) and acrylonitrile/buta- diene/styrene (ABS). Especially preferred are polyester and polyamide. More especially preferred are linear aromatic polyesters, which can be obtained by polycondensation of terephthalic acid and glycols, especially ethylene glycol, or condensation products of terephthalic acid and 1 ,4-bis(hydroxymethyl)cyclohexane, such as, for example, polyethylene terephthalate (PET) or polybutylene terephthalate (PBTP), and also polycarbonates, for example those obtained from α,α-dimethyI-4,4-dihydroxy- diphenylmethane and phosgene, or polymers based on polyvinyl chloride and on polyamide such as, for example, polyamide 6 or polyamide 6.6. The pigments according to the invention impart tinctorially strong shades to the above- mentioned materials, especially the polyester and polyamide materials, with very good in-use fastness properties, these especially being good light-fastness and good thermal stability.
The Examples that follow serve to illustrate the invention. Unless otherwise specified, parts therein are parts by weight and percentages are percentages by weight. The temperatures are given in degrees Celsius. The relationship between parts by weight and parts by volume is the same as that between grams and cubic centimetres.
Example 1:
10.2 parts of 2-indolinone are heated to 90° together with 14.3 parts of 3-iminoisoindolinone hydrochloride and 7.7 parts of potassium acetate in 100 parts of dioxane and 20 parts of glacial acetic acid and stirred at 90° for a further 4 hours. The reaction product that precipitates out is filtered off with suction and is washed with a 5:1 mixture of dioxane and glacial acetic acid and then water. After drying, 14.1 parts of the pigment of formula
Figure imgf000009_0001
are obtained, which colours polyester in the mass in yellow shades, with very good thermal stability and light-fastness.
Example 2:
4.4 parts of 2-cyanobenzamide are heated to 175° together with 4.1 parts of 2-indolinone in 25 parts of o-dichlorobenzene and stirred at that temperature for a further 6 hours. After cooling, 4.4 parts of the pigment of formula (100) precipitate out.
Example 3:
13.3 parts of 2-indolinone are dissolved in 300 parts of N,N-dimethylacetamide at room temperature and the resulting solution is added to a solution of 14.5 parts of diiminoisoindoline in 150 parts of N,N-dimethylacetamide at room temperature. On being left to stand for 48 hours and dilution with water, 25 parts of the pigment of formula
Figure imgf000010_0001
precipitate out.
1 part of the resulting product is stirred under reflux in 50 parts of 85 % acetic acid for 4 hours. After cooling, filtration and drying, 0.5 part of the pigment of formula (100) is isolated.
Example 4:
2.6 parts of the pigment of formula (101) prepared in Example 3 are stirred in a mixture of 70 parts of 98 % acetic acid and 10 parts of dimethylacetamide. After addition of 2 parts of dimedone, the reaction mixture is heated to 80° and is stirred at that temperature for a further 12 hours. After dilution with methanol, 2.7 parts of the pigment of formula
Figure imgf000010_0002
precipitate out, which colours polyester in the mass in red shades.
Examples 5-11 :
By replacing the 2.7 parts of dimedone in Example 4 with an equivalent amount of the active-methylene compound indicated in column 2 of Table 1 and proceeding as indicated in Example 4, pigments having the shades indicated in column 4 are likewise obtained. Tablel:
Figure imgf000011_0001
Figure imgf000012_0002
Examples 12-21:
By replacing the 14.3 parts of 3-iminoisoindolinone in Example 1 with an equivalent amount of the carbonyl or aldehyde compound indicated in column 2 of Table 2 and proceeding as indicated in Example 1 , pigments having the shades indicated in column 4 are likewise obtained.
Table 2:
Figure imgf000012_0001
Figure imgf000013_0001
Example 22:
5.2 parts of the pigment of formula (102) from Example 4 and 1 part of 1 ,4-phenylene- diamine are stirred under reflux in a mixture of 500 parts of ethanol and 50 parts of acetic acid for 24 hours. The precipitate is filtered off with suction and purified using a 1:1 mixture of dimethylformamide and acetone. 3.8 parts of the pigment of formula:
Figure imgf000014_0001
are obtained, which colours polyester in the mass in dark-red shades.
Colouring Example:
1200 parts of polyester granules (PET Arnite D04-300, DSM) are dried at 130°C for 4 hours and then mixed with 0.24 part of the pigment of formula
Figure imgf000014_0002
in a "roller rack" mixing apparatus at 60 revolutions per minute for 15 minutes, until homogeneous.
The homogeneous mixture is extruded in an extruder (twin screw 25 mm, from the company Collin, D-85560 Ebersberg) having 6 heating zones, at a maximum temperature of 275°C, cooled with water, granulated in a granulator (Turb Etuve TE 25 from the company MAPAG AG, CH-3001 Bern) and then dried at 130° for 4 hours, resulting in yellow-coloured polyester granules having good all-round fastness properties, especially having very good light and high-temperature-light fastness properties.

Claims

What is claimed is:
1. A pigment of formula
Figure imgf000015_0001
wherein
R., is hydrogen or C^C^alkyl, R2 is hydrogen, -CN, -COO-aryl, -COO-heteroaryl, -CONH-aryl or -CONH-heteroaryl, and R3 is the radical of a heteroaromatic compound of formula
Figure imgf000015_0002
Figure imgf000016_0001
or
R2 and R3 together form a radical of formula
Figure imgf000016_0002
wherein
R4 and R5 are each independently of the other -CN, -COO-aryl, -COO-heteroaryl,
-CONH-aryl or -CONH-heteroaryl, R6 is a radical of formula
Figure imgf000017_0001
R7 is halogen, and R8 and R9 are each independently of the other CrC4alkyl.
2. A pigment according to claim 1 , of formula
Figure imgf000017_0002
Figure imgf000018_0001
Figure imgf000018_0002
Figure imgf000019_0001
Figure imgf000020_0001
Figure imgf000021_0001
3. A process for the preparation of a pigment of formula (1) according to claim 1, which comprises reacting a compound of formula
Figure imgf000021_0002
wherein
X is =NH or =O, to form a compound of formula
Figure imgf000021_0003
and optionally, when X is =NH, further reacting the compound of formula (52) with an active- methylene compound, for example of formula R4 - CH2 - R5.
4. A method of producing coloured plastics or polymeric colour particles, which comprises mixing a high molecular weight organic material and a tinctorially effective amount of at least one pigment of formula (1) with one another.
5. A method of producing coloured plastics or polymeric colour particles, which comprises mixing a high molecular weight organic material and a tinctorially effective amount of at least one pigment of formulae (100) to (120) with one another.
6. Use of a pigment of formula (1) according to claim 1 in producing coloured plastics or polymeric colour particles.
7. Plastics or polymeric particles coloured with a pigment of formula (1) according to claim 1.
PCT/EP2003/001426 2002-02-21 2003-02-13 Lactam-based pigments and the use thereof in the production of coloured plastics or polymeric colour particles WO2003070830A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP2003569734A JP2005517792A (en) 2002-02-21 2003-02-13 Lactam-based pigments and their use in the production of colored plastic or polymeric colored particles
AU2003208847A AU2003208847A1 (en) 2002-02-21 2003-02-13 Lactam-based pigments and the use thereof in the production of coloured plastics or polymeric colour particles
US10/502,707 US7022177B2 (en) 2002-02-21 2003-02-13 Lactam-based pigments and the use thereof in the production of colored plastics or polymeric color particles
EP03706496A EP1476505B1 (en) 2002-02-21 2003-02-13 Lactam-based pigments and the use thereof in the production of coloured plastics or polymeric colour particles
KR10-2004-7013063A KR20040096601A (en) 2002-02-21 2003-02-13 Lactam-based pigments and the use thereof in the production of coloured plastics or polymeric colour particles
AT03706496T ATE553160T1 (en) 2002-02-21 2003-02-13 PIGMENTS BASED ON LACTAM AND THEIR USE IN THE PRODUCTION OF DYED PLASTIC OR POLYMERIC COLOR PARTICLES

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH2972002 2002-02-21
CH20020297/02 2002-02-21

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EP (1) EP1476505B1 (en)
JP (1) JP2005517792A (en)
KR (1) KR20040096601A (en)
CN (1) CN1636037A (en)
AT (1) ATE553160T1 (en)
AU (1) AU2003208847A1 (en)
WO (1) WO2003070830A1 (en)

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EP1424063A1 (en) * 2002-11-29 2004-06-02 L'oreal Cosmetic sunscreen compositions comprising 3-(2-azacycloalkylidene)-1,3-dihydro-indol-2-one derivatives and uses thereof

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WO2024166734A1 (en) * 2023-02-10 2024-08-15 富士フイルム株式会社 Colored composition, film, optical filter, solid-state imaging element, image display device, and compound

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* Cited by examiner, † Cited by third party
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EP1424063A1 (en) * 2002-11-29 2004-06-02 L'oreal Cosmetic sunscreen compositions comprising 3-(2-azacycloalkylidene)-1,3-dihydro-indol-2-one derivatives and uses thereof

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